JPH0357893B2 - - Google Patents
Info
- Publication number
- JPH0357893B2 JPH0357893B2 JP964883A JP964883A JPH0357893B2 JP H0357893 B2 JPH0357893 B2 JP H0357893B2 JP 964883 A JP964883 A JP 964883A JP 964883 A JP964883 A JP 964883A JP H0357893 B2 JPH0357893 B2 JP H0357893B2
- Authority
- JP
- Japan
- Prior art keywords
- present
- triphenylmethyl
- compound
- compounds
- ether
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- -1 thioester compound Chemical class 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 2
- XTECZMQXVKULBN-UHFFFAOYSA-N s-trityl 2-methylprop-2-enethioate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(SC(=O)C(=C)C)C1=CC=CC=C1 XTECZMQXVKULBN-UHFFFAOYSA-N 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003797 solvolysis reaction Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- JQZIKLPHXXBMCA-UHFFFAOYSA-N triphenylmethanethiol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(S)C1=CC=CC=C1 JQZIKLPHXXBMCA-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 1
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 1
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 229920001002 functional polymer Polymers 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000012690 ionic polymerization Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 125000003011 styrenyl group Chemical class [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- PTVDYMGQGCNETM-UHFFFAOYSA-N trityl 2-methylprop-2-enoate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(OC(=O)C(=C)C)C1=CC=CC=C1 PTVDYMGQGCNETM-UHFFFAOYSA-N 0.000 description 1
- MTAHZRMCRJONNA-UHFFFAOYSA-N trityl prop-2-enoate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(OC(=O)C=C)C1=CC=CC=C1 MTAHZRMCRJONNA-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
本発明は新規なチオエステル化合物に関する。
即ち、本発明は一般式
（式中、ＲはＨ又はCH3である）
で表わされる新規なチオエステル化合物を提供す
るものである。
本発明の化合物はビニル基を有するため重合及
び共重合が可能で有用な重合体を与えうるもので
ある。
本発明の化合物は、通常のチオエステルの合成
法を適用することにより合成することができる。
例えば、トリフエニルメチルメルカプタンをジエ
チルエーテル、テトラヒドロフラン等の溶媒に溶
解させ、これに等モルか若干過剰の水素化ナトリ
ウムを加えて反応させた後、トリフエニルメチル
メルカプタンに対して等モルか若干過剰のメタク
リル酸クロリド又は、アクリル酸クロリドを添加
することにより、本発明の化合物であるチオメタ
クリル酸Ｓ−トリフエニルメチル又はチオアクリ
ル酸Ｓ−トリフエニルメチルが容易に得られる。
本発明の化合物は、メタクリル酸トリフエニル
メチル又はアクリル酸トリフエニルメチルのよう
なエステル化合物と比較して、酸性および中性条
件下での加水分解速度ならびにアルコールによる
加溶媒分解速度が遅く、本発明の化合物を重合し
て得られた高分子物質も耐加水分解性、耐加溶媒
分解性に富むことが期待される。
本発明の化合物は、例えば光学活性なアニオン
重合開始剤を用いてイオン重合を行うと、光学活
性な重合体を与える。また、同様の方法でコモノ
マーとしてメタクリル酸トリフエニル等のメタク
リル酸エステルやアクリル酸エステル化合物と任
意の割合で共重合できる。さらにスチレン誘導
体、共役ジエン類等とはブロツク共重合体、グラ
フト共重合体を合成することが可能である。
得られた光学活性な高分子物質は、光学分割能
を持つ機能性ポリマーとして有用である。
次に本発明の化合物を実施例に沿つて詳述す
る。
実施例 １
トリフエニルメチルメルカプタン５ｇを、ジエ
チルエーテル60mlに溶かし、これに水素化ナトリ
ウム0.48ｇを０℃で加えた。生成したナトリウム
塩にメタクリル酸クロリド２ｇを添加し、75分反
応させた後、反応液に飽和炭酸ナトリウム水溶液
を加えてエーテルで抽出した。エーテル層を硫酸
マグネシウムで乾燥し、溶媒を留去した後、残渣
をエタノールで抽出し、不溶部を除いた。エタノ
ールを留去して得た粗生成物をエーテルより再結
晶した。収率1.5ｇ（24％）、融点120〜121℃。
チオメタクリル酸Ｓ−トリフエニルメチルであ
ることの確認は 1H−NMR、IRスペクトルおよ
び元素分析で行つた。
1H−NMR（100MHz、CCl4中、35℃）
α−CH3 δ1.83（ppm）
＝CH2 5.45、5.98
The present invention relates to novel thioester compounds. That is, the present invention is based on the general formula The present invention provides a novel thioester compound represented by the following formula: (wherein R is H or CH 3 ). Since the compound of the present invention has a vinyl group, it can be polymerized and copolymerized to give a useful polymer. The compound of the present invention can be synthesized by applying a conventional thioester synthesis method.
For example, triphenylmethyl mercaptan is dissolved in a solvent such as diethyl ether or tetrahydrofuran, and equimolar or slightly excess sodium hydride is added thereto and reacted. By adding methacrylic acid chloride or acrylic acid chloride, S-triphenylmethyl thiomethacrylate or S-triphenylmethyl thioacrylate, which is a compound of the present invention, can be easily obtained. The compounds of the present invention have a lower rate of hydrolysis under acidic and neutral conditions and a slower rate of solvolysis with alcohol than ester compounds such as triphenylmethyl methacrylate or triphenylmethyl acrylate, and the present invention It is expected that the polymeric substance obtained by polymerizing the compound will also have high hydrolysis resistance and solvolysis resistance. When the compound of the present invention is subjected to ionic polymerization using, for example, an optically active anionic polymerization initiator, an optically active polymer is obtained. Further, in a similar manner, it can be copolymerized with a methacrylic acid ester such as triphenyl methacrylate or an acrylic acid ester compound as a comonomer in any ratio. Furthermore, it is possible to synthesize block copolymers and graft copolymers with styrene derivatives, conjugated dienes, and the like. The obtained optically active polymer substance is useful as a functional polymer having optical resolution ability. Next, the compounds of the present invention will be described in detail with reference to Examples. Example 1 5 g of triphenylmethyl mercaptan was dissolved in 60 ml of diethyl ether, and 0.48 g of sodium hydride was added thereto at 0°C. After adding 2 g of methacrylic acid chloride to the generated sodium salt and reacting for 75 minutes, a saturated aqueous sodium carbonate solution was added to the reaction solution and extracted with ether. The ether layer was dried over magnesium sulfate, the solvent was distilled off, and the residue was extracted with ethanol to remove the insoluble portion. The crude product obtained by distilling off the ethanol was recrystallized from ether. Yield 1.5g (24%), melting point 120-121°C. The identity of the product as S-triphenylmethyl thiomethacrylate was confirmed by 1 H-NMR, IR spectrum, and elemental analysis. 1 H-NMR (100MHz, in CCl 4 , 35℃) α-CH 3 δ1.83 (ppm) = CH 2 5.45, 5.98
【式】 7.15 ●IR測定 Ｃ＝Ｏ 1670cm-1 Ｃ＝Ｃ 1625 ●元素分析 測定値 計算値（C23H20OS） Ｃ：80.21％ 80.20％ Ｈ：5.79 5.85 Ｓ： 9.31 9.31[Formula] 7.15 ●IR measurement C=O 1670cm -1 C=C 1625 ●Elemental analysis Measured value Calculated value (C 23 H 20 OS) C: 80.21% 80.20% H: 5.79 5.85 S: 9.31 9.31
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP964883A JPS59134776A (en) | 1983-01-24 | 1983-01-24 | Novel thioester compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP964883A JPS59134776A (en) | 1983-01-24 | 1983-01-24 | Novel thioester compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59134776A JPS59134776A (en) | 1984-08-02 |
| JPH0357893B2 true JPH0357893B2 (en) | 1991-09-03 |
Family
ID=11726030
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP964883A Granted JPS59134776A (en) | 1983-01-24 | 1983-01-24 | Novel thioester compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59134776A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10108634C2 (en) * | 2001-02-22 | 2003-12-18 | Siemens Ag | Electromechanical component |
| GB201003404D0 (en) * | 2010-03-01 | 2010-04-14 | Contamac Ltd | High refractive index polymer composition for opthalmic applications |
| US10155879B2 (en) | 2015-12-21 | 2018-12-18 | AZ Electronic Materials (Luxembourg) S.à.r.l. | Compositions and use thereof for modification of substrate surfaces |
-
1983
- 1983-01-24 JP JP964883A patent/JPS59134776A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59134776A (en) | 1984-08-02 |
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